Show/Hide Menu
Hide/Show Apps
Logout
Türkçe
Türkçe
Search
Search
Login
Login
OpenMETU
OpenMETU
About
About
Open Science Policy
Open Science Policy
Open Access Guideline
Open Access Guideline
Postgraduate Thesis Guideline
Postgraduate Thesis Guideline
Communities & Collections
Communities & Collections
Help
Help
Frequently Asked Questions
Frequently Asked Questions
Guides
Guides
Thesis submission
Thesis submission
MS without thesis term project submission
MS without thesis term project submission
Publication submission with DOI
Publication submission with DOI
Publication submission
Publication submission
Supporting Information
Supporting Information
General Information
General Information
Copyright, Embargo and License
Copyright, Embargo and License
Contact us
Contact us
Benzaldehyde lyase-catalyzed enantioselective carboligation of aromatic aldehydes with mono- and dimethoxy acetaldehyde
Download
index.pdf
Date
2003-06-12
Author
Demir, Ayhan Sıtkı
Sesenoglu, O
Dunkelmann, P
Muller, M
Metadata
Show full item record
This work is licensed under a
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
.
Item Usage Stats
252
views
165
downloads
Cite This
Benzaldehyde lyase from the Pseudomonas fluorescens catalyzes the reaction of aromatic aldehydes with methoxy and dimethoxy acetaldehyde and furnishes (R)-2-hydroxy-3-methoxy-1-arylpropan-1-one and (R)-2-hydroxy-3,3-dimethoxy-1-arylpropan-1-one in high yields and enantiomeric excess via acyloin linkage. Aromatic aldehydes and benzoins are converted into enamine-carbanion-like intermediates prior to carboligation.
Subject Keywords
Physical and Theoretical Chemistry
,
Organic Chemistry
,
Biochemistry
URI
https://hdl.handle.net/11511/53686
Journal
ORGANIC LETTERS
DOI
https://doi.org/10.1021/ol034415b
Collections
Department of Chemistry, Article
Suggestions
OpenMETU
Core
Benzaldehyde Lyase-Catalyzed Direct Amidation of Aldehydes with Nitroso Compounds
Ayhan, Peruze; Demir, Ayhan Sıtkı (Wiley, 2011-03-07)
Benzaldehyde lyase from the Pseudomonas fluorescens catalyzes the reaction of aromatic aldehydes with nitroso compounds and furnishes N-arylhydroxamic acids in high yields. Aromatic aldehydes and benzoins are converted into enamine-carbanion-like intermediates prior to their reaction with nitroso compounds. The kinetic resolution of rac-2-hydroxy-1,2-diphenylethanones furnished (S)-benzoins and arylhydroxamic acids with high enantioselectivities and conversions.
Functionalization of oxabenzonorbornadiene: Manganese(III)-mediated oxidative addition of dimedone
ÇALIŞKAN, Raşit; Sari, Ozlem; Balcı, Metin (Wiley, 2017-09-01)
3-Chloro-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-2-yl)-3-hydroxy-5,5-dimethylcy-clohex- 2-en-1-one, synthesized by the reaction of oxabenzonorbornadiene with Mn(OAc)(3) and dimedone in the presence of HCl in acetic acid, was submitted to ring-opening reactions with BBr3 and H2SO4. Reaction with BBr3 yielded 2 products, a 5-membered ring and an 8-membered ring, with the former being the major product. However, the H2SO4-supported reaction exclusively formed an 8-membered ring. The mechanism of formation of th...
Benzaldehyde lyase catalyzed enantioselective self and cross condensation reactions of acetaldehyde derivatives
Ayhan, Peruze; Turan, Ilke Simsek; Cifci, Burce; Demir, Ayhan Sıtkı (Royal Society of Chemistry (RSC), 2011-01-01)
Flexible protected 1,3,4-trihydroxy-2-butanone is synthesized in high enantiomeric excesses by using asymmetric homo- and cross- acyloin coupling of aliphatic aldehydes catalyzed by benzaldehyde lyase.
Organosilanols as Catalysts in Asymmetric Aryl Transfer Reactions
Özçubukçu, Salih; BOLM, Carsten (American Chemical Society (ACS), 2005-03-01)
Various ferrocene-based organosilanols have been synthesized in four steps starting from achiral ferrocene carboxylic acid. Applying these novel planar-chiral ferrocenes as catalysts in asymmetric phenyl transfer reactions to substituted benzaldehydes afforded products with high enantiomeric excesses. The best result (91% ee) was achieved in the addition to p-chlorobenzaldehyde with organosilanol 2b, which has a tert-butyl substituent on the oxazoline ring and an isopropyl group on the silanol fragment.
Fam-Ti catalyzed enantioselective alkynylation of aldehydes
KOYUNCU, Hasan; Doğan, Özdemir (American Chemical Society (ACS), 2007-08-16)
Ferrocenyl-substituted aziridinylmethanol (Fam-1) has been used as a chiral catalyst with titanium for enantioselective alkynylation of aromatic, heteroaromatic, aliphatic, and alpha,beta-unsaturated aldehydes to give the corresponding propargylic alcohols in up to 96% yield and 96% ee. The ligand can be prepared easily and recycled.
Citation Formats
IEEE
ACM
APA
CHICAGO
MLA
BibTeX
A. S. Demir, O. Sesenoglu, P. Dunkelmann, and M. Muller, “Benzaldehyde lyase-catalyzed enantioselective carboligation of aromatic aldehydes with mono- and dimethoxy acetaldehyde,”
ORGANIC LETTERS
, pp. 2047–2050, 2003, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/53686.